There is a temptation to think that selling a business begins when someone makes an offer.
It doesn’t.
It begins years earlier, in the thousands of small decisions founders make every day.
That was one of my biggest takeaways from a recent conversation with entrepreneur, investor and technology leader Matt O’Donovan on The Investor Circle Podcast.
Matt’s entrepreneurial journey is one many founders aspire to. He built Spark WiFi from a startup operating out of his garage into one of the UK’s leading managed Wi-Fi businesses before successfully selling the company during the uncertainty of the COVID period. He then spent five years working inside one of the world’s most active technology acquirers, giving him a rare opportunity to experience mergers and acquisitions from both sides of the table.
That perspective makes his advice particularly valuable.
Because he isn’t speaking as someone who has simply raised investment.
He’s speaking as someone who has built, sold, acquired and now invests.
Many first-time founders spend months refining their pitch deck.
Far fewer spend the same amount of time preparing themselves.
Matt explained that while products, markets and financial models matter, the first thing he evaluates is the founder.
Do they genuinely believe in the problem they’re solving?
Will they still be standing when the inevitable setbacks arrive?
Can they explain not only what they’re building, but why it deserves to exist?
These questions are surprisingly difficult to fake.
Experience teaches investors to recognise authenticity remarkably quickly.
One of the most honest moments in our conversation came when Matt reflected on selling his own company.
Like many founders, he wanted to present the business in the best possible light.
But experienced acquirers don’t simply listen.
They investigate.
Future revenue, customer pipelines, market assumptions and financial forecasts are all challenged in extraordinary detail. During due diligence, every optimistic assumption must eventually stand on evidence.
The lesson wasn’t that founders should undersell themselves.
It was that credibility becomes one of the most valuable assets a company owns.
Trust is surprisingly difficult to build.
It is incredibly easy to lose.
Naturally, our conversation turned towards artificial intelligence.
Today’s founders can build software faster than ever before.
Entire products that once required teams of engineers can now be developed in weeks.
That creates enormous opportunity.
It also creates enormous competition.
Matt’s observation was refreshingly practical.
If your business can be replicated quickly by a much larger organisation, where does your lasting advantage come from?
Increasingly, the answer isn’t simply software.
It is customer understanding.
Industry expertise.
Execution.
Relationships.
Operational excellence.
These remain difficult to automate.
Perhaps the most fascinating part of our discussion wasn’t about technology at all.
It was about people.
Companies are sold for remarkably different reasons.
Some founders have achieved everything they set out to do.
Some simply want a new challenge.
Others recognise that their business has outgrown their own experience.
And occasionally, founders are simply exhausted.
Every acquisition tells a human story before it tells a financial one.
That is easy to forget when headlines focus on valuations rather than journeys.
Towards the end of our conversation, I asked Matt what advice he would give someone raising investment for the first time.
His answer has stayed with me.
Know your why.
Not because investors enjoy hearing inspirational stories.
Because purpose shapes every decision that follows.
It influences resilience.
It influences culture.
It influences hiring.
It influences customers.
And ultimately, it influences whether investors believe you can build something that lasts.
If you’re building your first company, preparing to raise capital, or even considering becoming an angel investor yourself, I think you’ll enjoy this conversation.
Matt doesn’t offer shortcuts.
He offers something much more valuable.
Perspective earned through experience.
And those lessons are often the ones that save founders years of unnecessary mistakes.
If this article has sparked your curiosity, I encourage you to listen to the full episode. Many of Matt’s best stories, examples and reflections simply can’t be captured in writing. Hearing them in his own words brings a depth and authenticity that’s difficult to reproduce on the page.
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Guest: Matt O’Donovan
https://www.linkedin.com/in/mattodonovan/
Host: Stewart Noakes
https://www.linkedin.com/in/stewartnoakes/
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